(2E,6E)-2,6-Bis(2,5-difluoro-benzyl-idene)cyclo-hexa-none.

In the title compound, C(20)H(14)F(4)O, a derivative of curcumin, the dihedral angle between the two aromatic rings is 27.19 (13)°. The C=C double bonds have an E configuration.

Related literature

For background and related structures, see: Liang et al. (2007a ▶,b ▶, 2009 ▶); Zhao et al. (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C20H14F4O

M = 346.31

Monoclinic,

a = 15.824 (2) Å

b = 6.3128 (8) Å

c = 17.097 (2) Å

β = 111.756 (3)°

V = 1586.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.43 × 0.35 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.490, T max = 1.000

8935 measured reflections

3425 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.156

S = 0.93

3425 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011499/ng2751sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011499/ng2751Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H14F4O	F(000) = 712
Mr = 346.31	Dx = 1.450 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.824 (2) Å	Cell parameters from 1858 reflections
b = 6.3128 (8) Å	θ = 2.4–22.3°
c = 17.097 (2) Å	µ = 0.12 mm−1
β = 111.756 (3)°	T = 293 K
V = 1586.2 (3) Å3	Prismatic, colorless
Z = 4	0.43 × 0.35 × 0.27 mm

Bruker SMART CCD area-detector diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.049
phi and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→20
Tmin = 0.490, Tmax = 1.000	k = −7→8
8935 measured reflections	l = −21→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.082P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
3425 reflections	Δρmax = 0.23 e Å−3
227 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
F1	0.40753 (15)	0.4774 (3)	1.14644 (10)	0.1192 (7)
F2	0.42662 (12)	1.2350 (2)	1.00801 (10)	0.0934 (5)
F3	0.00929 (10)	0.5237 (2)	0.36811 (8)	0.0809 (5)
F4	0.16575 (11)	1.2677 (2)	0.49902 (9)	0.0839 (5)
O1	0.17234 (12)	1.1232 (3)	0.76698 (9)	0.0796 (6)
C1	0.20606 (14)	0.9520 (4)	0.76181 (12)	0.0520 (6)
C2	0.26784 (13)	0.8418 (3)	0.83949 (12)	0.0466 (5)
C3	0.29758 (14)	0.9609 (4)	0.90938 (13)	0.0556 (6)
H3	0.2766	1.0999	0.9033	0.067*
C4	0.35876 (14)	0.9001 (4)	0.99398 (12)	0.0528 (6)
C5	0.35519 (16)	0.7068 (4)	1.03101 (14)	0.0633 (6)
H5	0.3125	0.6053	1.0019	0.076*
C6	0.4149 (2)	0.6673 (5)	1.11059 (15)	0.0760 (8)
C7	0.47922 (18)	0.8090 (6)	1.15698 (15)	0.0836 (9)
H7	0.5196	0.7755	1.2108	0.100*
C8	0.48225 (18)	1.0026 (5)	1.12152 (16)	0.0794 (8)
H8	0.5247	1.1039	1.1512	0.095*
C9	0.42230 (17)	1.0439 (4)	1.04241 (14)	0.0654 (7)
C10	0.18662 (13)	0.8503 (3)	0.67808 (12)	0.0466 (5)
C11	0.14905 (14)	0.9764 (3)	0.61179 (13)	0.0517 (6)
H11	0.1403	1.1160	0.6244	0.062*
C12	0.11951 (13)	0.9273 (3)	0.52187 (12)	0.0470 (5)
C13	0.07950 (14)	0.7364 (3)	0.48623 (12)	0.0503 (5)
H13	0.0731	0.6275	0.5202	0.060*
C14	0.04988 (14)	0.7102 (4)	0.40128 (13)	0.0556 (6)
C15	0.05733 (15)	0.8634 (4)	0.34722 (14)	0.0614 (7)
H15	0.0367	0.8396	0.2895	0.074*
C16	0.09649 (17)	1.0538 (4)	0.38151 (14)	0.0629 (7)
H16	0.1025	1.1624	0.3472	0.076*
C17	0.12608 (15)	1.0796 (3)	0.46646 (14)	0.0562 (6)
C18	0.29633 (15)	0.6182 (3)	0.83255 (12)	0.0528 (6)
H18A	0.2525	0.5215	0.8405	0.063*
H18B	0.3549	0.5916	0.8769	0.063*
C19	0.30317 (15)	0.5754 (4)	0.74764 (12)	0.0541 (6)
H19A	0.3514	0.6616	0.7421	0.065*
H19B	0.3188	0.4279	0.7446	0.065*
C20	0.21500 (14)	0.6242 (3)	0.67610 (12)	0.0523 (6)
H20A	0.2220	0.5968	0.6230	0.063*
H20B	0.1677	0.5313	0.6796	0.063*

	U11	U22	U33	U12	U13	U23
F1	0.193 (2)	0.0997 (14)	0.0587 (9)	0.0260 (13)	0.0392 (11)	0.0185 (9)
F2	0.1281 (14)	0.0767 (12)	0.0776 (10)	−0.0307 (10)	0.0406 (10)	−0.0231 (8)
F3	0.0950 (11)	0.0712 (10)	0.0577 (8)	−0.0144 (8)	0.0066 (7)	−0.0117 (7)
F4	0.1145 (12)	0.0498 (9)	0.0738 (9)	−0.0116 (8)	0.0189 (9)	0.0087 (7)
O1	0.1081 (14)	0.0625 (12)	0.0539 (10)	0.0340 (10)	0.0133 (9)	−0.0087 (8)
C1	0.0591 (13)	0.0470 (14)	0.0464 (12)	0.0073 (11)	0.0155 (10)	−0.0066 (10)
C2	0.0484 (12)	0.0478 (13)	0.0427 (11)	−0.0004 (9)	0.0159 (9)	−0.0013 (9)
C3	0.0606 (14)	0.0549 (14)	0.0478 (12)	0.0038 (11)	0.0159 (11)	−0.0042 (10)
C4	0.0539 (12)	0.0624 (15)	0.0421 (11)	0.0039 (11)	0.0179 (10)	−0.0090 (10)
C5	0.0741 (16)	0.0689 (17)	0.0456 (12)	−0.0015 (13)	0.0206 (12)	−0.0073 (11)
C6	0.104 (2)	0.082 (2)	0.0416 (13)	0.0253 (16)	0.0262 (14)	0.0058 (13)
C7	0.0701 (17)	0.126 (3)	0.0422 (14)	0.0292 (18)	0.0062 (13)	−0.0182 (16)
C8	0.0680 (17)	0.109 (2)	0.0561 (16)	−0.0100 (16)	0.0176 (14)	−0.0303 (16)
C9	0.0707 (16)	0.0769 (19)	0.0497 (14)	−0.0028 (14)	0.0235 (13)	−0.0184 (13)
C10	0.0472 (11)	0.0444 (13)	0.0433 (11)	0.0023 (9)	0.0113 (9)	−0.0041 (9)
C11	0.0588 (13)	0.0431 (13)	0.0483 (12)	0.0081 (10)	0.0143 (10)	−0.0010 (9)
C12	0.0463 (11)	0.0458 (13)	0.0454 (11)	0.0090 (9)	0.0128 (9)	0.0046 (9)
C13	0.0536 (12)	0.0474 (13)	0.0445 (12)	0.0013 (10)	0.0118 (10)	0.0054 (9)
C14	0.0550 (13)	0.0537 (15)	0.0494 (13)	0.0027 (11)	0.0092 (10)	−0.0019 (11)
C15	0.0648 (15)	0.0728 (18)	0.0429 (12)	0.0142 (13)	0.0157 (11)	0.0048 (12)
C16	0.0729 (15)	0.0599 (16)	0.0547 (14)	0.0092 (13)	0.0221 (12)	0.0188 (12)
C17	0.0619 (14)	0.0417 (14)	0.0577 (14)	0.0045 (11)	0.0137 (11)	0.0063 (11)
C18	0.0606 (13)	0.0513 (14)	0.0437 (11)	0.0047 (11)	0.0161 (10)	0.0013 (10)
C19	0.0617 (13)	0.0494 (14)	0.0476 (12)	0.0110 (11)	0.0159 (10)	−0.0016 (10)
C20	0.0626 (13)	0.0462 (14)	0.0432 (11)	0.0059 (10)	0.0140 (10)	−0.0039 (9)

F1—C6	1.371 (3)	C10—C20	1.500 (3)
F2—C9	1.355 (3)	C11—C12	1.465 (3)
F3—C14	1.360 (2)	C11—H11	0.9300
F4—C17	1.362 (2)	C12—C17	1.381 (3)
O1—C1	1.223 (2)	C12—C13	1.392 (3)
C1—C10	1.493 (3)	C13—C14	1.361 (3)
C1—C2	1.497 (3)	C13—H13	0.9300
C2—C3	1.341 (3)	C14—C15	1.372 (3)
C2—C18	1.500 (3)	C15—C16	1.380 (3)
C3—C4	1.462 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.361 (3)
C4—C9	1.380 (3)	C16—H16	0.9300
C4—C5	1.386 (3)	C18—C19	1.519 (3)
C5—C6	1.361 (3)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—C7	1.366 (4)	C19—C20	1.508 (3)
C7—C8	1.373 (4)	C19—H19A	0.9700
C7—H7	0.9300	C19—H19B	0.9700
C8—C9	1.359 (3)	C20—H20A	0.9700
C8—H8	0.9300	C20—H20B	0.9700
C10—C11	1.331 (3)
O1—C1—C10	120.60 (18)	C13—C12—C11	124.00 (19)
O1—C1—C2	120.36 (18)	C14—C13—C12	119.5 (2)
C10—C1—C2	119.03 (19)	C14—C13—H13	120.2
C3—C2—C1	115.35 (19)	C12—C13—H13	120.2
C3—C2—C18	125.57 (18)	F3—C14—C13	118.2 (2)
C1—C2—C18	118.93 (17)	F3—C14—C15	118.3 (2)
C2—C3—C4	128.3 (2)	C13—C14—C15	123.5 (2)
C2—C3—H3	115.9	C14—C15—C16	117.7 (2)
C4—C3—H3	115.9	C14—C15—H15	121.2
C9—C4—C5	116.7 (2)	C16—C15—H15	121.2
C9—C4—C3	119.3 (2)	C17—C16—C15	118.7 (2)
C5—C4—C3	124.0 (2)	C17—C16—H16	120.6
C6—C5—C4	119.1 (2)	C15—C16—H16	120.6
C6—C5—H5	120.4	C16—C17—F4	117.7 (2)
C4—C5—H5	120.4	C16—C17—C12	124.4 (2)
C5—C6—C7	123.5 (3)	F4—C17—C12	117.9 (2)
C5—C6—F1	117.7 (3)	C2—C18—C19	111.88 (17)
C7—C6—F1	118.8 (2)	C2—C18—H18A	109.2
C6—C7—C8	117.8 (2)	C19—C18—H18A	109.2
C6—C7—H7	121.1	C2—C18—H18B	109.2
C8—C7—H7	121.1	C19—C18—H18B	109.2
C9—C8—C7	119.0 (3)	H18A—C18—H18B	107.9
C9—C8—H8	120.5	C20—C19—C18	111.50 (18)
C7—C8—H8	120.5	C20—C19—H19A	109.3
F2—C9—C8	118.3 (2)	C18—C19—H19A	109.3
F2—C9—C4	117.9 (2)	C20—C19—H19B	109.3
C8—C9—C4	123.8 (3)	C18—C19—H19B	109.3
C11—C10—C1	115.29 (19)	H19A—C19—H19B	108.0
C11—C10—C20	126.35 (18)	C10—C20—C19	111.77 (17)
C1—C10—C20	118.28 (17)	C10—C20—H20A	109.3
C10—C11—C12	129.4 (2)	C19—C20—H20A	109.3
C10—C11—H11	115.3	C10—C20—H20B	109.3
C12—C11—H11	115.3	C19—C20—H20B	109.3
C17—C12—C13	116.12 (19)	H20A—C20—H20B	107.9
C17—C12—C11	119.8 (2)
O1—C1—C2—C3	−13.6 (3)	C2—C1—C10—C20	11.5 (3)
C10—C1—C2—C3	166.2 (2)	C1—C10—C11—C12	−178.3 (2)
O1—C1—C2—C18	170.6 (2)	C20—C10—C11—C12	5.2 (4)
C10—C1—C2—C18	−9.7 (3)	C10—C11—C12—C17	−146.9 (2)
C1—C2—C3—C4	−179.3 (2)	C10—C11—C12—C13	36.8 (4)
C18—C2—C3—C4	−3.8 (4)	C17—C12—C13—C14	0.1 (3)
C2—C3—C4—C9	141.8 (2)	C11—C12—C13—C14	176.5 (2)
C2—C3—C4—C5	−40.8 (4)	C12—C13—C14—F3	−178.60 (18)
C9—C4—C5—C6	−1.8 (3)	C12—C13—C14—C15	0.2 (3)
C3—C4—C5—C6	−179.3 (2)	F3—C14—C15—C16	178.34 (19)
C4—C5—C6—C7	0.1 (4)	C13—C14—C15—C16	−0.5 (4)
C4—C5—C6—F1	177.8 (2)	C14—C15—C16—C17	0.5 (4)
C5—C6—C7—C8	1.1 (4)	C15—C16—C17—F4	179.0 (2)
F1—C6—C7—C8	−176.6 (2)	C15—C16—C17—C12	−0.2 (4)
C6—C7—C8—C9	−0.5 (4)	C13—C12—C17—C16	0.0 (3)
C7—C8—C9—F2	−179.5 (2)	C11—C12—C17—C16	−176.6 (2)
C7—C8—C9—C4	−1.4 (4)	C13—C12—C17—F4	−179.30 (18)
C5—C4—C9—F2	−179.4 (2)	C11—C12—C17—F4	4.1 (3)
C3—C4—C9—F2	−1.7 (3)	C3—C2—C18—C19	−143.7 (2)
C5—C4—C9—C8	2.5 (4)	C1—C2—C18—C19	31.7 (3)
C3—C4—C9—C8	−179.8 (2)	C2—C18—C19—C20	−56.2 (3)
O1—C1—C10—C11	14.5 (3)	C11—C10—C20—C19	140.9 (2)
C2—C1—C10—C11	−165.28 (19)	C1—C10—C20—C19	−35.6 (3)
O1—C1—C10—C20	−168.7 (2)	C18—C19—C20—C10	58.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.93	2.46	3.343 (3)	158